What Is 4-Bromo-6-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile?

4-Bromo-6-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile is a bicyclic heterocyclic compound belonging to the pyrazolo[1,5-a]pyridine family. Its structure consists of a fused pyrazole–pyridine ring system substituted with a bromine atom at the C-4 position, a methoxy group at the C-6 position, and a nitrile (carbonitrile) group at the C-3 position. This combination of functional groups makes it a versatile and reactive scaffold for further chemical elaboration.

The pyrazolo[1,5-a]pyridine core is a privileged heterocyclic scaffold in drug discovery because it mimics purine-like hydrogen-bonding geometry and offers favorable drug-like physicochemical properties. The bromo substituent serves as a handle for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), the methoxy group modulates electron density and lipophilicity, and the nitrile group can be converted to a range of functional groups including amidines, tetrazoles, and primary amines.

Physicochemical Properties and Handling

As a halogenated aromatic nitrile, 4-bromo-6-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile is expected to be a solid at room temperature with moderate stability under standard laboratory conditions. The compound should be handled with appropriate personal protective equipment (PPE), including gloves, eye protection, and a laboratory coat, as aromatic nitriles and aryl bromides may be irritants.

The compound should be stored in a cool, dry, well-ventilated location away from moisture and light. Prolonged exposure to air and humidity may lead to degradation. It is recommended to keep the container tightly sealed and to aliquot the material if repeated access is required. Specific melting point, solubility, and spectral data (NMR, HRMS) should be confirmed against the certificate of analysis (CoA) provided with each lot.

Note: Exact physicochemical values (molecular weight, melting point, solubility) should be verified from the product CoA or a peer-reviewed source before use in critical applications.

Applications in Synthetic and Medicinal Chemistry

The compound serves primarily as a synthetic building block. The C-4 bromo group is well-suited for palladium-catalyzed cross-coupling reactions, enabling the introduction of aryl, heteroaryl, vinyl, or amino groups to diversify the core scaffold. The C-3 nitrile can undergo nucleophilic addition, cycloaddition (e.g., [3+2] to form tetrazoles), or reduction to yield aminomethyl derivatives, providing additional vectors for structural modification.

Pyrazolo[1,5-a]pyridine-containing compounds have been investigated in the literature as kinase inhibitors, adenosine receptor ligands, and CNS-active agents, making this scaffold relevant to drug discovery programs targeting such biological pathways. The methoxy group at C-6 provides an additional site for late-stage diversification via demethylation to a phenol followed by O-alkylation or O-arylation.

Disclaimer: Specific biological activity data for this exact compound are not confirmed in the source material. Users should conduct their own literature searches and biological evaluations.

Ordering and Quality Information

4-Bromo-6-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile is available from Aladdin Scientific under SKU B630732. To place an order, visit the Aladdin Scientific website, search by product name or SKU, select the required quantity, and proceed through the standard checkout process. Institutional purchase orders and bulk inquiries can be directed to the Aladdin Scientific sales team.

Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by HPLC or NMR), lot number, and key physicochemical data. Customers are encouraged to review the CoA upon receipt and to contact technical support if the material does not meet specifications. Purity grades and available pack sizes may vary; please check the current product listing on the website for up-to-date availability and pricing.